"Malie.” I mutter the Hawaiian word for “calm” before I giant-stride from the boat into the dark, one hand on my mask, the other clutching a flashlight. Splash. Salt stings my lips, which are all but swallowing my breathing regulator. The dark Pacific embraces me, the faint light from a retreating sun no longer in play. I flash my light into the black abyss. The local report of a 14-foot tiger shark invades my thoughts and my Zen-like plan to channel the spiritual Uncle Earl, manager of Hualalai Resort’s cultural center (tigers are “gods” to Hawaiians he explained), is suddenly waylaid. I look up at the boat and to my best friend and dive buddy, Gina, and give her the OK signal. She long-strides to me, and our dive master follows. We all deflate our BCs, and down we go.

Just 24 hours prior we are surveying this same stretch of sea from a plane, touching down at Kona International Airport via a direct flight from Phoenix. After a 10-minute drive past black lava fields and the 8,271-foot volcanic mountain of Hualalai, our driver alerts us to the 13,796-foot Mauna Kea before pulling into the confines of Hualalai Resort, located on the Big Island of Hawaii’s North Kona Kohala Coast. Struck with the native landscaping and Hawaiian fauna, we sip guava juice and I quickly feel a sense of ease. I’ve always been curious about The Big Island’s mystique. More specifically, I’m determined to uncover just why, come off-season, Hualalai Resort is on the itinerary of so many Aspenites.

We’ve assumed the resort’s Four Seasons hotel, which has the highest occupancy of all the brand’s global properties, to be the focal point of the gated grounds. But as we wind past an impossibly manicured golf course, rows of neatly stacked villas, townhomes, and ultraluxe homes, we quickly realize this community is much bigger than expected, though the Hawaiian architecture lends an intimate vibe. Nestled on 865 acres, the resort is owned by the Rockpoint Group and MSD Capital, Michael Dell’s investment firm, and is known to attract celebs, CEOs, and international tastemakers.

Once at our villa we’re personally escorted through a two-bedroom haven of Hawaiian culture. All of Hualalai’s villas (from $1.9 million to buy or $1,325–$6,500 per night to rent) and custom-built homes (from $4.6 million to $14.9 million) are wholly owned, and the owners of this particular unit surround its guests with an authentic nod to island culture. Our temporary respite has it all: gourmet kitchen, a beautiful outdoor shower off the master suite (as is custom here) and Four Seasons linens and bath amenities for those properties under Hualalai Villas & Homes management. But the kicker is the view. The navy Hawaiian Pacific comes into sharp focus as we walk onto a gorgeous outdoor living space, from which we can easily glimpse the island of Maui, just 30 miles away.

A quick change from travel shoes to flip-flops and we’re off to explore the grounds on our appointed golf cart, the preferred mode of transport. First up, a glass of Champagne, of course. With the sounds of native birds and the scent of hibiscus marking our path, we make our way to the Beach Tree restaurant at the Four Seasons. Jack Johnson’s “Bubble Toes” serenades a tony crowd as we sip our own version of bubbly and munch on the most delicious ahi carpaccio I’ve ever had. Alas, vacation has formally begun. As the ocean breeze tickles my nose and I toast my dear friend, it’s apparent why this special stretch of the globe is hyped.

A beachside lounging spot with a sunset view

One of Hualalai Resort’s custombuilt homes

An arial view of the resort, located 10 minutes from the town of Kona

Next up is a tour of the grounds courtesy of Violet Terawaki, Hualalai Resort’s marketing manager. As we golf-cart from mauna to makai, or from mountain to ocean, she explains the resort is “really about the place, the people who work here, and the activities. There’s an intimate sense of community.” Cute little goats cross the golf course as Terawaki takes us through beautifully constructed community neighborhoods to a large herb garden and the resort’s own fish farm, which harvests moi and shrimp.

We dine at the Residents’ Beach House restaurant, rebuilt after the 2010 tsunami, and a prime locale to watch the sunset. The aforementioned Uncle Earl (aka Earl Kamakaonaona Rigador), somewhat of an island legend, joins us. In his sixties but looking like he’s barely 45, his playful eyes hint he knows something you’d be lucky to learn. He’s a second-generation Hawaiian, extremely proud of his ancestry, has an encyclopedic knowledge of the Hawaiian Islands, and plays the ukulele. It’s the Uncle Earls of the property that keep the families returning and perpetuate a tangible sense of place.

The following morning welcomes a spa visit. On my way, I serendipitously run into part-time Aspenite Amy Phelan, fresh off the busy Aspen summer fundraising circuit and overdue for some R&R. Upon check-in, I’m greeted with herbal-infused hibiscus tea and my Australian therapist, Dani, leads me to Hualalai Spa’s signature apothecary. I’ve chosen the Hulali (Sparkle) Apothecary Treatment, and as Dani explains the native oils, herbs and flowers to customize my body scrub, it all smells so delicious that my chosen formula is robust: passion fruit and coconut lemongrass oils mixed with lavender, jasmine, coconut, and hibiscus, complemented by a bamboo salt base, a coffee accent, a hint of ginger, and a rice-bran binder. With that I’m whisked away to a private indoor-outdoor treatment room. Between Dani’s expert lomi lomi massage, the exotic scrub, and the warmth of the Hawaiian sun as I shower in the outdoor lanai, any lingering worries have vanished into the island air.

After a lunch of mahi tacos, white sangria, and homemade rocky mountain road ice cream (indulgence is a theme here, after all) I meet Aspenites Carolyn and Ken Hamlet at their Hualalai home. They, too, have just arrived from a busy season in Aspen, and Carolyn, who is the founder of Hamlet Financial Corporation and serves on the boards of both the Aspen Art Museum and the Anderson Ranch Arts Center, is buzzing with the excitement of island life. As a mother of two, for her, Hualalai’s appeal is about family. As she tours me through her art-filled compound, she explains, “We can’t think of a better place to split our time. Our son Bryce learned to play tennis and golf here, and there are great swim instructors. It’s the equivalent of what you have in Aspen with the outdoor ed. It gives kids self-confidence.” The Bakers, also from Aspen, are set to arrive that evening to stay with the Hamlets, and Carolyn is prepping for their visit.

My visit with Carolyn is cut short, but for good reason, which is to experience the aforementioned night scuba dive in hopes of a visit from the island’s playful manta rays. Alas, we are skunked on the rays, but once our nerves calm and we’re safely scouting a beautiful reef, it’s an adventure like none other. Afterward we toast our bravery with Coronas at a local dive bar, where massive halibut are being cleaned on the porch. Back at the resort, our bartender overindulges us with a fleet of wine samples so we can order just the right Syrah. (Tip for oenophiles: Every wine on the list is offered by the glass.)

Inspiration on the oceanfront jogging path

Our last day on the island is action-packed. A stand-up paddle lesson is the first order of the morning, and as Gina and I call on our inner Laird Hamilton, we survey the calm, clear water for the elusive mantas. My water journey continues with a two-man canoe trip that follows the coastline and is surprisingly efficient, thanks to a well-toned Hawaiian guide. The afternoon finds us on a threehour guided hike on Hualalai Mountain (offered to Hualalai guests and homeowners). We drive past Charles Schwab’s own private golf course, and once on foot, our guide leads us directly to the mouth of the volcano that formed Hualalai Mountain. We each take turns hovering over this gaping, powerful chasm, silent and awe-struck. At the hike’s end, which winds into actual lava tubes, we turn our headlamps off, surrounded by complete darkness.

With just four hours to departure, we spend our time wisely at the adult-only Palm Grove Pool and swim-up bar. While sipping $18 yuzu and pineapple specialty margaritas (be prepared for pricey but oh-so-tasty cocktails) we spy a cowboy hat-clad Hilary Swank, sunbathing with what looks to be a movie script. She makes her way to the pool, beau by her side, and they’re seemingly akin to any other cozy couple on vacation. Eventually she swims up to the bar and is chatty, explaining she clumsily mixed pool water with her cocktail and needs a redo. Yes, life’s easy here.

Fresh-of-the-boat sushi ends our day before we begrudgingly acknowledge the time has come for real world reentry. On our walk back to the villa the stars are brilliant, and we discuss how on our next visit we must check out the observatory atop Mauna Kea, considered the best place in the world for stargazing. And while en route to the airport, as if on cue, our mellow cabbie mentions the night’s stars, too. “Such a calm night,” he remarks. Malai, indeed.